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Hydrochloric Acid → 2-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamide

HRID 750361
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 750361
[C:1]([C:9]1[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:10]=1[C:11]([N:13]([CH2:25][CH:26]([OH:30])[CH2:27][CH2:28][CH3:29])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O.Cl>CS(C)=O>[C:1]([C:9]1[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:10]=1[C:11]([N:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:19][CH:20]=1)[CH2:25][C:26](=[O:30])[CH2:27][CH2:28][CH3:29])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 230607862-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide

Produkt 1

HCID 230608192-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamideAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

[Step 2] To a solution of 2-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide (2.7 g) in DMSO (27 ml) was added triethylamine (11 ml), and pyridine sulfur trioxide complex (6.2 g) was added to the mixture at room temperature. The mixture was stirred for 1 hr. and added to water. 10% Hydrochloric acid was added to acidify the aqueous layer and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 2-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamide (2.2 g).

Aufarbeitung

  1. additionwas added to the mixture at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-239edc06f2ef4dfba4c32b4d04da959c
Quelldatensatz
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07402595B2

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